Tetrahydrofuran → HCID 69381053, compound

Participants

Reaction Steps

A solution of methallylchloride (0.692 g, 7.64 mmol) in freshly distilled tetrahydrofuran (THF) (2.5 mL) was added to a suspension of flame-dried Mg metal turnings (0.28 g, 11.5 mmol) in THF (2.5 mL) over 30 minutes at 60° C. The resulting Grignard solution darkened during heating at reflux for an additional 20 minutes. The mixture was then cooled to −42° C. (dry ice/chlorobenzene bath), and a solution of the enone Compound 3 (0.4182 g, 2.6 mmol) in THF (2.5 mL) was added dropwise. After 5 minutes, the cooling bath was removed, and the reaction was stirred for 1.5 hours as it warmed to room temperature. The mixture was then decanted into ice-cold 0.1 N HCl (50 mL) and extracted with ether. The combined organic fractions were washed with water and brine, dried over Na2SO4, filtered, and concentrated. Column chromatography (with 90:10/Hexane: EtOAc) provided Compound 4a (0.52 g, 92% yield) as a colorless liquid. 1H NMR: (250 MHz, CDCl3), δ 0.973 (s 3H), 1.05–1.01 (d 1H), 1.21 (s 3H), 1.60–1.57 (d of t, 3H), 1.61 (s 3H), 1.92 (s 3H), 2.63–2.18 (m 5H), 4.82–4.65 (m 2H), 5.79–5.77 (m 1H); 13C NMR (62.5 MHz, CDCl3) δ 13.1, 22.4, 24.7, 27.3, 30.1, 31.6, 37.9, 38.7, 48.9, 49.8, 78.7, 114.4, 122.0, 143.2, 143.4.

Provenance & Evidence